This happened a few years ago when I was a college senior. I interned for a marketing company because it paid a little but I had no interest at all in the work. My supervisor, Hailey, was in her mid 20s, not that much older than me. There were four of us interns but we worked in different parts of the building so it was kind of lonely and boring most of the time.
Hailey and I hit it off, though, and were jokey with each other. She was a cute blonde and had gorgeous breasts. I had to always work hard to keep up eye contact with her so she wouldn’t think I was staring at her tits.
At the end of the internship, she and a few other employees took all of us interns out for dinner. Most everyone left after that, but a few of us decided to grab drinks at a nearby bar. Finally, it was just me and Hailey sitting on two stools at the end of the bar. She told me she needed to know if I was ever going to try to come back to the company. I told her no, that I could care less about marketing.
“Good,” she said. She then slid her hand on my jeans and rested them there. “I’m not your boss anymore.”
“You want to go somewhere else for a drink?” I asked her. I could feel myself getting hard and she had to notice with her hand only inches from my dick.
“Sure,” she said. We left the bar and started walking, but the next place we ran into was crowded so I suggested we grab some beers at a convenience store and head back to my place since it was only about a ten minute walk away. She agreed and even reached out to hold my hand while we walked.
“I had a crush on you since the first day you started,” she said.
I told her I did, too. It was the longest walk of my life as I had a raging hard-on the whole way. As soon as we got inside my apartment, she closed the door and kissed me. Before I knew it, she was down on her knees undoing my belt.
“I’m glad I already did your performance evaluation,” she said before she took my cock in her mouth. I moaned a little and leaned back against the wall.
She stopped for a second and smiled up at me. “How do I rate as a boss?”
“Pretty fucking good!” I told her. I dropped the six-pack on an end table and pulled her back up to her feet where we kissed again as I started unbuttoning her shirt. She undid her bra while I started sliding her skirt off. Reaching for her underwear, I could tell she was super wet. Hailey moaned a little as I teased my fingers across the outside of her panties.
“You have condoms?” she asked.
I ran into my bedroom, grabbed one, and returned to find her on all fours by the door.
“I want you inside me,” she said. After getting the condom on, I slid inside her, my hands resting on her ass. It was still a bit surreal to go from seeing her everyday and fantasizing about what she was like naked to getting to pound her from behind. She told me to pull her hair, which I did, and I kept fucking her like that until she closed her legs together and laid flat on the carpet. She was so tight at that point, I couldn’t last another second and told her I was cumming. As soon as I did, I felt her squeeze tight around me and start spasming too.
I laid next to her on the floor and she snuggled up against me. After a long silence, she told me I was a “naughty boy.” She then laughed as she saw me starting getting hard again. We fucked again, this time in the bedroom before we got a shower together. I offered to let her spend the night but she took an uber instead.
I still remember every detail of that night because it was the hottest sex of my life. It’s been fodder for my jerk-off fantasies for awhile now. Hailey and I stayed in touch for awhile but didn’t have sex again because she moved across the country a few months later.
Source: reddit.com/r/gonewildstories/comments/svnbfx/mf_i_was_an_intern_who_got_to_fuck_my_former_boss